IL152942A - Compounds 2 - Ethyl and 2 - Ethylaidine - 19 - Nur - Vitamin D and pharmaceutical preparations containing them - Google Patents

Compounds 2 - Ethyl and 2 - Ethylaidine - 19 - Nur - Vitamin D and pharmaceutical preparations containing them

Info

Publication number: IL152942A
Authority: IL; Israel
Prior art keywords: dihydroxyvitamin; ethylidene; ethyl; pharmaceutical composition; compound
Prior art date: 2000-05-31

Application number

IL152942A

Other languages

English (en)

Hebrew (he)

Other versions

IL152942A0 (en

Original Assignee

Wisconsin Alumni Res Found

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-05-31

Filing date

2001-05-31

Publication date

2007-09-20

2001-05-31 Application filed by Wisconsin Alumni Res Found filed Critical Wisconsin Alumni Res Found

2003-06-24 Publication of IL152942A0 publication Critical patent/IL152942A0/xx

2007-09-20 Publication of IL152942A publication Critical patent/IL152942A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 52
-1 2 - ethyl Chemical group 0.000 title description 34
150000001875 compounds Chemical class 0.000 claims abstract description 101
210000000988 bone and bone Anatomy 0.000 claims abstract description 9
208000029725 Metabolic bone disease Diseases 0.000 claims abstract description 3
229960005084 calcitriol Drugs 0.000 claims description 107
239000000203 mixture Substances 0.000 claims description 38
239000003814 drug Substances 0.000 claims description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
201000010099 disease Diseases 0.000 claims description 21
238000004519 manufacturing process Methods 0.000 claims description 12
208000001132 Osteoporosis Diseases 0.000 claims description 9
238000007911 parenteral administration Methods 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
238000011200 topical administration Methods 0.000 claims description 9
GMRQFYUYWCNGIN-UHFFFAOYSA-N 1,25-Dihydroxy-vitamin D3' Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CC(O)C1=C GMRQFYUYWCNGIN-UHFFFAOYSA-N 0.000 claims description 8
201000004384 Alopecia Diseases 0.000 claims description 5
231100000360 alopecia Toxicity 0.000 claims description 5
201000004624 Dermatitis Diseases 0.000 claims description 4
201000004681 Psoriasis Diseases 0.000 claims description 4
150000003431 steroids Chemical group 0.000 claims description 3
201000001320 Atherosclerosis Diseases 0.000 claims description 2
206010006187 Breast cancer Diseases 0.000 claims description 2
208000026310 Breast neoplasm Diseases 0.000 claims description 2
208000013725 Chronic Kidney Disease-Mineral and Bone disease Diseases 0.000 claims description 2
206010009944 Colon cancer Diseases 0.000 claims description 2
206010020649 Hyperkeratosis Diseases 0.000 claims description 2
206010020772 Hypertension Diseases 0.000 claims description 2
208000013038 Hypocalcemia Diseases 0.000 claims description 2
208000000038 Hypoparathyroidism Diseases 0.000 claims description 2
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
208000001126 Keratosis Diseases 0.000 claims description 2
206010060862 Prostate cancer Diseases 0.000 claims description 2
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
206010039984 Senile osteoporosis Diseases 0.000 claims description 2
208000010668 atopic eczema Diseases 0.000 claims description 2
230000008416 bone turnover Effects 0.000 claims description 2
208000029742 colonic neoplasm Diseases 0.000 claims description 2
206010012601 diabetes mellitus Diseases 0.000 claims description 2
230000002500 effect on skin Effects 0.000 claims description 2
230000036571 hydration Effects 0.000 claims description 2
238000006703 hydration reaction Methods 0.000 claims description 2
230000000705 hypocalcaemia Effects 0.000 claims description 2
210000000987 immune system Anatomy 0.000 claims description 2
208000032839 leukemia Diseases 0.000 claims description 2
206010025135 lupus erythematosus Diseases 0.000 claims description 2
201000006417 multiple sclerosis Diseases 0.000 claims description 2
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206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
210000002374 sebum Anatomy 0.000 claims description 2
230000028327 secretion Effects 0.000 claims description 2
230000037393 skin firmness Effects 0.000 claims description 2
230000037303 wrinkles Effects 0.000 claims description 2
208000030136 Marchiafava-Bignami Disease Diseases 0.000 claims 1
206010052779 Transplant rejections Diseases 0.000 claims 1
239000011575 calcium Substances 0.000 abstract description 17
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 abstract description 17
230000000694 effects Effects 0.000 abstract description 14
229910052791 calcium Inorganic materials 0.000 abstract description 13
238000011282 treatment Methods 0.000 abstract description 13
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 9
230000000968 intestinal effect Effects 0.000 abstract description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 8
PKFBWEUIKKCWEW-WEZTXPJVSA-N (1r,3r)-5-[(2e)-2-[(1r,3as,7ar)-1-[(2r)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]cyclohexane-1,3-diol Chemical group C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1C[C@@H](O)C[C@H](O)C1 PKFBWEUIKKCWEW-WEZTXPJVSA-N 0.000 abstract description 7
230000024245 cell differentiation Effects 0.000 abstract description 6
238000001727 in vivo Methods 0.000 abstract description 4
230000001483 mobilizing effect Effects 0.000 abstract description 3
206010065687 Bone loss Diseases 0.000 abstract description 2
QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 39
239000011710 vitamin D Substances 0.000 description 28
229940046008 vitamin d Drugs 0.000 description 28
229930003316 Vitamin D Natural products 0.000 description 25
235000019166 vitamin D Nutrition 0.000 description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
150000003710 vitamin D derivatives Chemical group 0.000 description 15
239000011647 vitamin D3 Substances 0.000 description 15
229940021056 vitamin d3 Drugs 0.000 description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
229910052799 carbon Inorganic materials 0.000 description 14
235000005282 vitamin D3 Nutrition 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 12
238000000034 method Methods 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
229940088594 vitamin Drugs 0.000 description 12
239000011782 vitamin Substances 0.000 description 12
QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 12
238000009472 formulation Methods 0.000 description 10
229930003231 vitamin Natural products 0.000 description 9
235000013343 vitamin Nutrition 0.000 description 9
239000007788 liquid Substances 0.000 description 7
239000004480 active ingredient Substances 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
230000008878 coupling Effects 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
239000005556 hormone Substances 0.000 description 6
229940088597 hormone Drugs 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000000243 solution Substances 0.000 description 6
102000009310 vitamin D receptors Human genes 0.000 description 6
108050000156 vitamin D receptors Proteins 0.000 description 6
241000700159 Rattus Species 0.000 description 5
125000002252 acyl group Chemical group 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
230000027455 binding Effects 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 5
230000003389 potentiating effect Effects 0.000 description 5
230000008569 process Effects 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
230000032258 transport Effects 0.000 description 5
ATMUYWZMPLKPEJ-XLMAVXFVSA-N (1r,3ar,7ar)-7a-methyl-1-[(2r)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-one Chemical compound O=C1CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@H]21 ATMUYWZMPLKPEJ-XLMAVXFVSA-N 0.000 description 4
238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 4
238000007239 Wittig reaction Methods 0.000 description 4
238000003556 assay Methods 0.000 description 4
230000000125 calcaemic effect Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
125000001153 fluoro group Chemical group F* 0.000 description 4
230000006870 function Effects 0.000 description 4
150000002431 hydrogen Chemical group 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
230000009467 reduction Effects 0.000 description 4
230000004044 response Effects 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000000725 suspension Substances 0.000 description 4
MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 4
229960003783 24-homo-1,25-dihydroxyvitamin d3 Drugs 0.000 description 3
KJKIIUAXZGLUND-ICCVIKJNSA-N 25-hydroxyvitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](\C=C\[C@H](C)C(C)(C)O)C)=C\C=C1\C[C@@H](O)CCC1=C KJKIIUAXZGLUND-ICCVIKJNSA-N 0.000 description 3
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
MECHNRXZTMCUDQ-UHFFFAOYSA-N Vitamin D2 Natural products C1CCC2(C)C(C(C)C=CC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C MECHNRXZTMCUDQ-UHFFFAOYSA-N 0.000 description 3
125000004183 alkoxy alkyl group Chemical group 0.000 description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
244000309464 bull Species 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000006071 cream Substances 0.000 description 3
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 3
238000010511 deprotection reaction Methods 0.000 description 3
229910052805 deuterium Inorganic materials 0.000 description 3
230000004069 differentiation Effects 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
229960002061 ergocalciferol Drugs 0.000 description 3
239000012634 fragment Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000002674 ointment Substances 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 3
210000004765 promyelocyte Anatomy 0.000 description 3
230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
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235000001892 vitamin D2 Nutrition 0.000 description 3
239000011653 vitamin D2 Substances 0.000 description 3
VJIOBQLKFJUZJB-IBOOZMTFSA-N (1r,3ar,7ar)-1-[(e,2r,5r)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-one Chemical compound O=C1CCC[C@]2(C)[C@@H]([C@H](C)/C=C/[C@H](C)C(C)C)CC[C@H]21 VJIOBQLKFJUZJB-IBOOZMTFSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 2
DIPPFEXMRDPFBK-UHFFFAOYSA-N Vitamin D4 Natural products C1CCC2(C)C(C(C)CCC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C DIPPFEXMRDPFBK-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
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GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 2
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JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000001962 taste-modifying agent Substances 0.000 description 2
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DIPPFEXMRDPFBK-JPWDPSJFSA-N vitamin D4 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CC[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C DIPPFEXMRDPFBK-JPWDPSJFSA-N 0.000 description 2
150000003722 vitamin derivatives Chemical class 0.000 description 2
AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
JWUBBDSIWDLEOM-UHFFFAOYSA-N 25-Hydroxycholecalciferol Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CCC1=C JWUBBDSIWDLEOM-UHFFFAOYSA-N 0.000 description 1
JWUBBDSIWDLEOM-DCHLRESJSA-N 25-Hydroxyvitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C/C=C1\C[C@@H](O)CCC1=C JWUBBDSIWDLEOM-DCHLRESJSA-N 0.000 description 1
JWUBBDSIWDLEOM-NQZHSCJISA-N 25-hydroxy-3 epi cholecalciferol Chemical compound C1([C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=CC=C1C[C@H](O)CCC1=C JWUBBDSIWDLEOM-NQZHSCJISA-N 0.000 description 1
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POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 description 1
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OBTIDFCSHQLONE-UHFFFAOYSA-N diphenylphosphane;lithium Chemical compound [Li].C=1C=CC=CC=1PC1=CC=CC=C1 OBTIDFCSHQLONE-UHFFFAOYSA-N 0.000 description 1
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238000006345 epimerization reaction Methods 0.000 description 1
150000002137 ergosterols Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000035876 healing Effects 0.000 description 1
238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
239000000865 liniment Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000000302 molecular modelling Methods 0.000 description 1
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
102000006255 nuclear receptors Human genes 0.000 description 1
108020004017 nuclear receptors Proteins 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
230000011164 ossification Effects 0.000 description 1
125000003431 oxalo group Chemical group 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000000926 separation method Methods 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000007070 tosylation reaction Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000011995 wilkinson's catalyst Substances 0.000 description 1

Classifications

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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
- A61K31/593—9,10-Secocholestane derivatives, e.g. cholecalciferol, i.e. vitamin D3
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/18—Drugs for disorders of the endocrine system of the parathyroid hormones
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Physical Education & Sports Medicine (AREA)
Diabetes (AREA)
Rheumatology (AREA)
Epidemiology (AREA)
Immunology (AREA)
Hematology (AREA)
Orthopedic Medicine & Surgery (AREA)
Dermatology (AREA)
Endocrinology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Transplantation (AREA)
Neurology (AREA)
Obesity (AREA)
Pain & Pain Management (AREA)
Neurosurgery (AREA)
Emergency Medicine (AREA)
Biomedical Technology (AREA)
Reproductive Health (AREA)
Vascular Medicine (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL152942A 2000-05-31 2001-05-31 Compounds 2 - Ethyl and 2 - Ethylaidine - 19 - Nur - Vitamin D and pharmaceutical preparations containing them IL152942A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US20819900P	2000-05-31	2000-05-31
PCT/US2001/017662 WO2001092221A1 (en)	2000-05-31	2001-05-31	2-ethyl and 2-ethylidene-19-nor-vitamin d compounds

Publications (2)

Publication Number	Publication Date
IL152942A0 IL152942A0 (en)	2003-06-24
IL152942A true IL152942A (en)	2007-09-20

Family

ID=22773624

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL152942A IL152942A (en)	2000-05-31	2001-05-31	Compounds 2 - Ethyl and 2 - Ethylaidine - 19 - Nur - Vitamin D and pharmaceutical preparations containing them

Country Status (15)

Country	Link
US (5)	US6806262B2 (de)
EP (1)	EP1286962B1 (de)
JP (1)	JP4022141B2 (de)
AT (1)	ATE399151T1 (de)
AU (2)	AU2001265272B2 (de)
BR (1)	BR0111173A (de)
CA (1)	CA2410880C (de)
DE (1)	DE60134549D1 (de)
DK (1)	DK1286962T3 (de)
ES (1)	ES2309069T3 (de)
IL (1)	IL152942A (de)
MX (1)	MXPA02011820A (de)
NZ (1)	NZ522909A (de)
PT (1)	PT1286962E (de)
WO (1)	WO2001092221A1 (de)

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US20030018017A1 (en) *	2001-01-25	2003-01-23	Deluca Hector F.	Method of treatment of type I diabetes
BR0307896A (pt) *	2002-03-29	2004-12-07	Wisconsin Alumni Res Found	Método de produção de 1(alfa)-hidroxi-2-metileno-19-nor-homopregnacalcif erol
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EP1559708A4 (de) *	2002-10-10	2006-07-19	Wisconsin Alumni Res Found	2,2-disubstituiertes 1a,25-dihydroxy-19-norvitamin-d-derivat
WO2004067504A1 (ja) *	2003-01-31	2004-08-12	Chugai Seiyaku Kabushiki Kaisha	２位置換ビタミンｄ誘導体
WO2004076468A1 (ja)	2003-02-25	2004-09-10	Kobe Tennenbutsu Kagaku Kabushiki Kaisha	ビタミンｄ誘導体を合成するための新規な中間体
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BRPI0409194A (pt) *	2003-04-10	2006-04-11	Wisconsin Alumni Res Found	compostos, composição farmacêutica e método de tratamento de doença metabólica do osso, da psorìase, da leucemia, cáncer do cólon, cáncer da mama, cáncer da pele ou cáncer da próstata, de doença auto-imune, de doença inflamatória do intestino e de aumento da resistência do osso
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AU2004266706B2 (en) *	2003-08-20	2009-07-30	Wisconsin Alumni Research Foundation	2-methylene-19-nor-vitamin D2 compounds
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US7214670B2 (en) *	2003-09-24	2007-05-08	Wisconsin Alumni Research Foundation	Use of 2-methylene-19-nor-20(S)-1α,25-dihydroxyvitamin D3 to increase the life expectancy of human beings
US7704980B2 (en) *	2003-10-08	2010-04-27	Wisconsin Alumni Research Foundation	Treatment of inflammatory bowel disease with 2-methylene-19-nor-vitamin D compounds
US8404667B2 (en) *	2006-12-29	2013-03-26	Wisconsin Alumni Research Foundation	Compounds, compositions, kits and methods of use to orally and topically treat acne and other skin conditions by 19-Nor vitamin D analog
US7713951B2 (en) *	2004-04-09	2010-05-11	Wisconsin Alumni Research Foundation	2-alkylidene-18,19-dinor-vitamin D compounds
CA2586679A1 (en)	2004-11-12	2006-05-18	Bioxell Spa	Combined use of vitamin d derivatives and anti-proliferative agents for treating bladder cancer
CA2588412A1 (en) *	2004-11-22	2006-06-01	Wisconsin Alumni Research Foundation	2alpha-methyl-19-nor-1alpha-hydroxy-homopregnacalciferol and its uses
AU2005309804B9 (en) *	2004-11-22	2011-12-08	Wisconsin Alumni Research Foundation	2alpha-methyl-19-nor-(20S)-1alpha-hydroxy-bishomopregnacalciferol and its uses
JP5161582B2 (ja) *	2004-11-22	2013-03-13	ウィスコンシン・アルムニ・リサーチ・ファウンデーション	１７，２０（ｚ）−デヒドロビタミンｄ類似体およびそれらの使用
ATE467614T1 (de) *	2004-11-22	2010-05-15	Wisconsin Alumni Res Found	2-methylen-19,26,27-trinor-(20s)-1-alpha- hydroxyvitamin d3 and dessen verwendungen
JP2008520689A (ja)	2004-11-22	2008-06-19	ウィスコンシン・アルムニ・リサーチ・ファウンデーション	１９，２６，２７−トリノル−（２０Ｓ）−１α−ヒドロキシビタミンＤ３の２α−メチルおよび２β−メチル類似体およびそれらの使用
CA2605727A1 (en) *	2005-05-03	2006-11-09	Wisconsin Alumni Research Foundation	19,26,27-trinor-1.alpha.,25-dihydroxyvitamin d3 compounds
US7803789B2 (en) *	2006-02-02	2010-09-28	Wisconsin Alumni Research Foundation	Vitamin D analog—RAK, methods and uses thereof
US7528122B2 (en) *	2006-02-02	2009-05-05	Wisconsin Alumni Research Foundation	Vitamin D analog—NEL, methods and uses thereof
US20090281340A1 (en) *	2006-04-05	2009-11-12	Deluca Hector F	1alpha-hydroxy-2-(3'-hydroxypropylidene)-19-nor-vitamin d compounds and methods of making and treatment thereof
EP2010483A2 (de)	2006-04-05	2009-01-07	Wisconsin Alumni Research Foundation	1.alpha.-hydroxy-2-(3'-hydroxypropyliden)-19-nor-vitamin-d-verbindungen sowie verfahren zu ihrer herstellung und verwendung
MX2008012671A (es) *	2006-04-06	2008-10-15	Wisconsin Alumni Res Found	Analogos 1 a,25-dihidroxi- 19, 26,27-trinor vitamina d 2-sustituidos y sus usos.
US7648973B2 (en) *	2006-04-06	2010-01-19	Wisconsin Alumni Research Foundation	2-methylene-1α,25-dihydroxy-19,21-dinorvitamin D3 analogs and uses thereof
JP2009533483A (ja) *	2006-04-06	2009-09-17	ウイスコンシンアラムニリサーチファンデーション	２−メチレン−１α，２５−ジヒドロキシ−１８，１９，２１−トリノルビタミンＤ３およびその使用
MX2009003241A (es) *	2006-09-28	2009-05-05	Wisconsin Alumni Res Found	Analogos de 2-metilen-(20r,25s)-19,27-dinor-(22e)-vitamina d.
ATE552238T1 (de) *	2006-09-28	2012-04-15	Wisconsin Alumni Res Found	2-methylen-(20s,25s)-19,27-dinor-(22e)-vitamin- - analoga
US7893043B2 (en) *	2008-07-10	2011-02-22	Wisconsin Alumni Research Foundation	2-methylene-(17Z)-17(20)-dehydro-19,21-dinor-vitamin D analogs
US7888339B2 (en) *	2008-07-10	2011-02-15	Wisconsin Alumni Research Foundation	2-methylene-20(21)-dehydro-19-nor-vitamin D analogs
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2001
- 2001-05-31 US US09/871,227 patent/US6806262B2/en not_active Expired - Lifetime
- 2001-05-31 MX MXPA02011820A patent/MXPA02011820A/es active IP Right Grant
- 2001-05-31 DE DE60134549T patent/DE60134549D1/de not_active Expired - Lifetime
- 2001-05-31 AT AT01939792T patent/ATE399151T1/de active
- 2001-05-31 IL IL152942A patent/IL152942A/en not_active IP Right Cessation
- 2001-05-31 EP EP01939792A patent/EP1286962B1/de not_active Expired - Lifetime
- 2001-05-31 PT PT01939792T patent/PT1286962E/pt unknown
- 2001-05-31 AU AU2001265272A patent/AU2001265272B2/en not_active Ceased
- 2001-05-31 DK DK01939792T patent/DK1286962T3/da active
- 2001-05-31 CA CA002410880A patent/CA2410880C/en not_active Expired - Fee Related
- 2001-05-31 JP JP2002500836A patent/JP4022141B2/ja not_active Expired - Lifetime
- 2001-05-31 NZ NZ522909A patent/NZ522909A/en not_active IP Right Cessation
- 2001-05-31 WO PCT/US2001/017662 patent/WO2001092221A1/en not_active Ceased
- 2001-05-31 BR BR0111173-6A patent/BR0111173A/pt not_active Application Discontinuation
- 2001-05-31 ES ES01939792T patent/ES2309069T3/es not_active Expired - Lifetime
- 2001-05-31 AU AU6527201A patent/AU6527201A/xx active Pending
2004
- 2004-10-01 US US10/957,483 patent/US6992074B2/en not_active Expired - Lifetime
2005
- 2005-07-28 US US11/191,791 patent/US7141558B2/en not_active Expired - Lifetime
2006
- 2006-11-22 US US11/603,721 patent/US7300925B2/en not_active Expired - Lifetime
2007
- 2007-08-16 US US11/839,586 patent/US7468361B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US6806262B2 (en)	2004-10-19
ES2309069T3 (es)	2008-12-16
IL152942A0 (en)	2003-06-24
CA2410880A1 (en)	2001-12-06
ATE399151T1 (de)	2008-07-15
PT1286962E (pt)	2008-07-30
BR0111173A (pt)	2003-04-29
US7141558B2 (en)	2006-11-28
DK1286962T3 (da)	2008-10-06
JP2004501114A (ja)	2004-01-15
US20050043281A1 (en)	2005-02-24
DE60134549D1 (de)	2008-08-07
AU2001265272B2 (en)	2006-08-17
US7468361B2 (en)	2008-12-23
JP4022141B2 (ja)	2007-12-12
US20080032956A1 (en)	2008-02-07
EP1286962B1 (de)	2008-06-25
US6992074B2 (en)	2006-01-31
EP1286962A1 (de)	2003-03-05
WO2001092221A1 (en)	2001-12-06
US7300925B2 (en)	2007-11-27
US20030013691A1 (en)	2003-01-16
AU6527201A (en)	2001-12-11
NZ522909A (en)	2004-09-24
MXPA02011820A (es)	2003-04-10
CA2410880C (en)	2009-03-03
US20050282789A1 (en)	2005-12-22
US20070088008A1 (en)	2007-04-19

Legal Events

Date	Code	Title
2008-02-10	FF	Patent granted
2008-04-13	KB	Patent renewed
2015-04-30	KB	Patent renewed
2019-12-31	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP1286962B1 (de)	2008-06-25	2-ethyl und 2-ethyliden-19-nor-vitamin d-verbindungen
AU2001265272A1 (en)	2002-02-28	2-ethyl and 2-ethylidene-19-nor-vitamin D compounds
EP0971888B1 (de)	2003-10-29	2-alkyl-19-nor-vitamin d-verbindungen
EP0970047B1 (de)	2002-09-11	2-alkyliden-19-nor-vitamin d-verbindungen
JP4493340B2 (ja)	2010-06-30	１α−ヒドロキシ−２−メチレン−１９−ノル−プレグナカルシフェロール及びその使用
WO1998041500A9 (en)	1999-03-04	2-alkyl-19-nor-vitamin d compounds
NZ522160A (en)	2004-11-26	2-alkylidene-19-nor-vitamin D compounds and their therapeutic uses
AU2001247873A1 (en)	2002-01-03	26,27-homologated-20-epi-2-alkyl-19-nor-vitamin D compounds
EP1268415A1 (de)	2003-01-02	26,27-homologierte-20-epi-2-alkyl-19-nor-vitamin d-verbindungen
AU2004266706B2 (en)	2009-07-30	2-methylene-19-nor-vitamin D2 compounds
US5962707A (en)	1999-10-05	19-nor-vitamin D3 compounds with calcemic activity
EP1524264A2 (de)	2005-04-20	2-Ethyliden-19-Nor-Vitamin D-Verbindungen
AU2002360534B2 (en)	2007-05-03	1-alpha-hydroxy-2-methylene-19-nor-pregnacalciferol and its uses